DE69605452T2 - Alkyl(hetero)cyclische Derivate, Verfahren zu deren Herstellung und sie enthaltende pharmazeutische Zusammensetzungen - Google Patents
Alkyl(hetero)cyclische Derivate, Verfahren zu deren Herstellung und sie enthaltende pharmazeutische ZusammensetzungenInfo
- Publication number
- DE69605452T2 DE69605452T2 DE69605452T DE69605452T DE69605452T2 DE 69605452 T2 DE69605452 T2 DE 69605452T2 DE 69605452 T DE69605452 T DE 69605452T DE 69605452 T DE69605452 T DE 69605452T DE 69605452 T2 DE69605452 T2 DE 69605452T2
- Authority
- DE
- Germany
- Prior art keywords
- formula
- ethyl
- compounds
- group
- alkyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- 125000000217 alkyl group Chemical group 0.000 title claims abstract description 51
- 238000002360 preparation method Methods 0.000 title claims description 37
- 238000000034 method Methods 0.000 title claims description 35
- 125000004122 cyclic group Chemical group 0.000 title claims description 3
- 125000005842 heteroatom Chemical group 0.000 title description 4
- 239000008194 pharmaceutical composition Substances 0.000 title 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 20
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims abstract description 17
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims abstract description 15
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims abstract description 10
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 8
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 8
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 8
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims abstract description 7
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 7
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims abstract description 7
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims abstract description 7
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims abstract description 6
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 6
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 claims abstract description 6
- KEIFWROAQVVDBN-UHFFFAOYSA-N 1,2-dihydronaphthalene Chemical compound C1=CC=C2C=CCCC2=C1 KEIFWROAQVVDBN-UHFFFAOYSA-N 0.000 claims abstract description 5
- 125000003884 phenylalkyl group Chemical group 0.000 claims abstract description 4
- YJUFGFXVASPYFQ-UHFFFAOYSA-N 2,3-dihydro-1-benzothiophene Chemical compound C1=CC=C2SCCC2=C1 YJUFGFXVASPYFQ-UHFFFAOYSA-N 0.000 claims abstract description 3
- 125000004043 oxo group Chemical group O=* 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 159
- 229910052739 hydrogen Inorganic materials 0.000 claims description 26
- 229910052757 nitrogen Inorganic materials 0.000 claims description 18
- 238000011282 treatment Methods 0.000 claims description 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
- 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 8
- 230000001193 melatoninergic effect Effects 0.000 claims description 8
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 8
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 150000002367 halogens Chemical class 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- CFHGBZLNZZVTAY-UHFFFAOYSA-N lawesson's reagent Chemical compound C1=CC(OC)=CC=C1P1(=S)SP(=S)(C=2C=CC(OC)=CC=2)S1 CFHGBZLNZZVTAY-UHFFFAOYSA-N 0.000 claims description 6
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 6
- 230000001575 pathological effect Effects 0.000 claims description 6
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 6
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 6
- 208000019116 sleep disease Diseases 0.000 claims description 5
- 208000013738 Sleep Initiation and Maintenance disease Diseases 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 4
- 208000035475 disorder Diseases 0.000 claims description 4
- 230000002526 effect on cardiovascular system Effects 0.000 claims description 4
- 125000001041 indolyl group Chemical group 0.000 claims description 4
- 206010022437 insomnia Diseases 0.000 claims description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 4
- 239000001301 oxygen Chemical group 0.000 claims description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
- 208000012672 seasonal affective disease Diseases 0.000 claims description 4
- 208000027559 Appetite disease Diseases 0.000 claims description 3
- 208000019454 Feeding and Eating disease Diseases 0.000 claims description 3
- 208000008589 Obesity Diseases 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000001624 naphthyl group Chemical group 0.000 claims description 3
- 235000020824 obesity Nutrition 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 125000004434 sulfur atom Chemical group 0.000 claims description 3
- 125000006528 (C2-C6) alkyl group Chemical group 0.000 claims description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 235000019253 formic acid Nutrition 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 150000002475 indoles Chemical class 0.000 claims description 2
- 150000002476 indolines Chemical class 0.000 claims description 2
- 239000000463 material Substances 0.000 claims description 2
- JFXQEUDWGJKZNK-UHFFFAOYSA-N n-[2-(7-ethyl-1,2,3,4-tetrahydronaphthalen-1-yl)ethyl]-2,2,2-trifluoroacetamide Chemical compound C1CCC(CCNC(=O)C(F)(F)F)C2=CC(CC)=CC=C21 JFXQEUDWGJKZNK-UHFFFAOYSA-N 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- 125000001475 halogen functional group Chemical group 0.000 abstract 2
- 101100516554 Caenorhabditis elegans nhr-5 gene Proteins 0.000 abstract 1
- 241000689227 Cora <basidiomycete fungus> Species 0.000 abstract 1
- 125000000592 heterocycloalkyl group Chemical group 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 42
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 39
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 38
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 30
- 125000003118 aryl group Chemical group 0.000 description 25
- -1 methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, tert-butoxy, pentyloxy Chemical group 0.000 description 25
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 22
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 21
- 239000000376 reactant Substances 0.000 description 21
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 20
- 230000000694 effects Effects 0.000 description 20
- 238000002844 melting Methods 0.000 description 18
- 230000008018 melting Effects 0.000 description 18
- 238000003756 stirring Methods 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 17
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 16
- 238000012844 infrared spectroscopy analysis Methods 0.000 description 16
- 230000033764 rhythmic process Effects 0.000 description 15
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 14
- 238000004611 spectroscopical analysis Methods 0.000 description 14
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 13
- 150000001408 amides Chemical class 0.000 description 13
- 150000001555 benzenes Chemical class 0.000 description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 239000003480 eluent Substances 0.000 description 12
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
- 241001465754 Metazoa Species 0.000 description 11
- 239000000428 dust Substances 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 10
- 239000002253 acid Substances 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 9
- 239000012346 acetyl chloride Substances 0.000 description 9
- 230000008034 disappearance Effects 0.000 description 9
- 238000000921 elemental analysis Methods 0.000 description 9
- 238000001953 recrystallisation Methods 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 8
- 238000004440 column chromatography Methods 0.000 description 8
- 235000011167 hydrochloric acid Nutrition 0.000 description 8
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 8
- 235000019341 magnesium sulphate Nutrition 0.000 description 8
- 239000012074 organic phase Substances 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 8
- 239000000460 chlorine Substances 0.000 description 7
- 229910052801 chlorine Inorganic materials 0.000 description 7
- 239000012230 colorless oil Substances 0.000 description 7
- 239000002244 precipitate Substances 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 102000001419 Melatonin receptor Human genes 0.000 description 6
- 108050009605 Melatonin receptor Proteins 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 6
- 239000008346 aqueous phase Substances 0.000 description 6
- 229960003987 melatonin Drugs 0.000 description 6
- 239000012528 membrane Substances 0.000 description 6
- 229910000027 potassium carbonate Inorganic materials 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- YJPIGAIKUZMOQA-UHFFFAOYSA-N Melatonin Natural products COC1=CC=C2N(C(C)=O)C=C(CCN)C2=C1 YJPIGAIKUZMOQA-UHFFFAOYSA-N 0.000 description 5
- 230000006978 adaptation Effects 0.000 description 5
- 238000010640 amide synthesis reaction Methods 0.000 description 5
- 230000027455 binding Effects 0.000 description 5
- 239000012948 isocyanate Substances 0.000 description 5
- 150000002513 isocyanates Chemical class 0.000 description 5
- DRLFMBDRBRZALE-UHFFFAOYSA-N melatonin Chemical compound COC1=CC=C2NC=C(CCNC(C)=O)C2=C1 DRLFMBDRBRZALE-UHFFFAOYSA-N 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 230000000144 pharmacologic effect Effects 0.000 description 5
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 241000287828 Gallus gallus Species 0.000 description 4
- 241000699670 Mus sp. Species 0.000 description 4
- 241001494479 Pecora Species 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 241000700159 Rattus Species 0.000 description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- 230000000740 bleeding effect Effects 0.000 description 4
- 238000011835 investigation Methods 0.000 description 4
- 239000003446 ligand Substances 0.000 description 4
- 239000012280 lithium aluminium hydride Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 229910000069 nitrogen hydride Inorganic materials 0.000 description 4
- 229920000137 polyphosphoric acid Polymers 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- AQRLNPVMDITEJU-UHFFFAOYSA-N triethylsilane Chemical compound CC[SiH](CC)CC AQRLNPVMDITEJU-UHFFFAOYSA-N 0.000 description 4
- HWONSBWFASAZNW-UHFFFAOYSA-N 2-(5-ethyl-1-benzothiophen-3-yl)acetonitrile Chemical compound CCC1=CC=C2SC=C(CC#N)C2=C1 HWONSBWFASAZNW-UHFFFAOYSA-N 0.000 description 3
- BEPHOZUYBNZPSS-UHFFFAOYSA-N 2-(5-ethyl-1-benzothiophen-3-yl)ethanamine Chemical compound CCC1=CC=C2SC=C(CCN)C2=C1 BEPHOZUYBNZPSS-UHFFFAOYSA-N 0.000 description 3
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 3
- KWMBADTWRIGGGG-UHFFFAOYSA-N 2-diethoxyphosphorylacetonitrile Chemical compound CCOP(=O)(CC#N)OCC KWMBADTWRIGGGG-UHFFFAOYSA-N 0.000 description 3
- ZLHLIRYSBPOFQB-UHFFFAOYSA-N 4-(4-ethylphenyl)-4-oxobutanoic acid Chemical compound CCC1=CC=C(C(=O)CCC(O)=O)C=C1 ZLHLIRYSBPOFQB-UHFFFAOYSA-N 0.000 description 3
- WWQQPHUHTAZWDH-UHFFFAOYSA-N 4-ethylbenzenethiol Chemical compound CCC1=CC=C(S)C=C1 WWQQPHUHTAZWDH-UHFFFAOYSA-N 0.000 description 3
- 208000024827 Alzheimer disease Diseases 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 101100311330 Schizosaccharomyces pombe (strain 972 / ATCC 24843) uap56 gene Proteins 0.000 description 3
- 239000005864 Sulphur Substances 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N acetonitrile Substances CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 230000000949 anxiolytic effect Effects 0.000 description 3
- 210000003169 central nervous system Anatomy 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- JFWMYCVMQSLLOO-UHFFFAOYSA-N cyclobutanecarbonyl chloride Chemical compound ClC(=O)C1CCC1 JFWMYCVMQSLLOO-UHFFFAOYSA-N 0.000 description 3
- XWBDWHCCBGMXKG-UHFFFAOYSA-N ethanamine;hydron;chloride Chemical compound Cl.CCN XWBDWHCCBGMXKG-UHFFFAOYSA-N 0.000 description 3
- XFYFBTGDESEZAZ-UHFFFAOYSA-N ethyl 2-(5-ethyl-1-benzothiophen-3-yl)acetate Chemical compound C1=C(CC)C=C2C(CC(=O)OCC)=CSC2=C1 XFYFBTGDESEZAZ-UHFFFAOYSA-N 0.000 description 3
- OHLRLMWUFVDREV-UHFFFAOYSA-N ethyl 4-chloro-3-oxobutanoate Chemical compound CCOC(=O)CC(=O)CCl OHLRLMWUFVDREV-UHFFFAOYSA-N 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 230000006742 locomotor activity Effects 0.000 description 3
- 238000004949 mass spectrometry Methods 0.000 description 3
- FJDDSMSDZHURBJ-XSBOKVBDSA-N n-[2-(2-iodanyl-5-methoxy-1h-indol-3-yl)ethyl]acetamide Chemical compound COC1=CC=C2NC([125I])=C(CCNC(C)=O)C2=C1 FJDDSMSDZHURBJ-XSBOKVBDSA-N 0.000 description 3
- PICRXJDULXLJCZ-UHFFFAOYSA-N n-[2-(5-ethyl-1-benzothiophen-3-yl)ethyl]acetamide Chemical compound CCC1=CC=C2SC=C(CCNC(C)=O)C2=C1 PICRXJDULXLJCZ-UHFFFAOYSA-N 0.000 description 3
- XIJUDYSKBKSFNU-UHFFFAOYSA-N o-ethyl 4-(4-ethylphenyl)-3-oxobutanethioate Chemical compound CCOC(=S)CC(=O)CC1=CC=C(CC)C=C1 XIJUDYSKBKSFNU-UHFFFAOYSA-N 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 101150018444 sub2 gene Proteins 0.000 description 3
- 229940014800 succinic anhydride Drugs 0.000 description 3
- 239000003826 tablet Substances 0.000 description 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 2
- QBWBUCRCWAMNAO-UHFFFAOYSA-N 2-(5-ethyl-1-benzothiophen-3-yl)acetamide Chemical compound CCC1=CC=C2SC=C(CC(N)=O)C2=C1 QBWBUCRCWAMNAO-UHFFFAOYSA-N 0.000 description 2
- OFGMWYXMXTYADH-UHFFFAOYSA-N 2-(5-ethyl-1-benzothiophen-3-yl)acetic acid Chemical compound CCC1=CC=C2SC=C(CC(O)=O)C2=C1 OFGMWYXMXTYADH-UHFFFAOYSA-N 0.000 description 2
- PYOUAIQXJALPKW-UHFFFAOYSA-N 2-(5-methyl-1H-indol-3-yl)ethanamine Chemical compound CC1=CC=C2NC=C(CCN)C2=C1 PYOUAIQXJALPKW-UHFFFAOYSA-N 0.000 description 2
- CXWUTHWDNWQACQ-UHFFFAOYSA-N 2-(7-ethyl-1,2,3,4-tetrahydronaphthalen-1-yl)ethanamine Chemical compound C1CCC(CCN)C2=CC(CC)=CC=C21 CXWUTHWDNWQACQ-UHFFFAOYSA-N 0.000 description 2
- IDXWSFCOUZYCMF-UHFFFAOYSA-N 4-(4-ethylphenyl)butanoic acid Chemical compound CCC1=CC=C(CCCC(O)=O)C=C1 IDXWSFCOUZYCMF-UHFFFAOYSA-N 0.000 description 2
- LACFLXDRFOQEFZ-UHFFFAOYSA-N 4-ethylbenzenesulfonyl chloride Chemical compound CCC1=CC=C(S(Cl)(=O)=O)C=C1 LACFLXDRFOQEFZ-UHFFFAOYSA-N 0.000 description 2
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 2
- BMHUHOFPKFAGAR-UHFFFAOYSA-N 7-ethyl-3,4-dihydro-2h-naphthalen-1-one Chemical compound C1CCC(=O)C2=CC(CC)=CC=C21 BMHUHOFPKFAGAR-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N Cyclohexylamine Natural products NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- 206010028980 Neoplasm Diseases 0.000 description 2
- 208000018737 Parkinson disease Diseases 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 239000007868 Raney catalyst Substances 0.000 description 2
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- YADDAWIENYJSBL-UHFFFAOYSA-N n-[2-[5-(cyclopropylmethyl)-1-benzothiophen-3-yl]ethyl]pentanamide Chemical compound C1=C2C(CCNC(=O)CCCC)=CSC2=CC=C1CC1CC1 YADDAWIENYJSBL-UHFFFAOYSA-N 0.000 description 1
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- 231100000252 nontoxic Toxicity 0.000 description 1
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- 239000002674 ointment Substances 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 208000019906 panic disease Diseases 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 229940127557 pharmaceutical product Drugs 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- SSOLNOMRVKKSON-UHFFFAOYSA-N proguanil Chemical compound CC(C)\N=C(/N)N=C(N)NC1=CC=C(Cl)C=C1 SSOLNOMRVKKSON-UHFFFAOYSA-N 0.000 description 1
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- 201000000980 schizophrenia Diseases 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
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- 235000012239 silicon dioxide Nutrition 0.000 description 1
- XGVXKJKTISMIOW-ZDUSSCGKSA-N simurosertib Chemical compound N1N=CC(C=2SC=3C(=O)NC(=NC=3C=2)[C@H]2N3CCC(CC3)C2)=C1C XGVXKJKTISMIOW-ZDUSSCGKSA-N 0.000 description 1
- DDMGAAYEUNWXSI-XVSDJDOKSA-M sodium;(5z,8z,11z,14z)-icosa-5,8,11,14-tetraenoate Chemical compound [Na+].CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC([O-])=O DDMGAAYEUNWXSI-XVSDJDOKSA-M 0.000 description 1
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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Classifications
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/02—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
- C07C233/08—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with carbon atoms of carboxamide groups bound to acyclic carbon atoms of a saturated carbon skeleton containing rings
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P9/06—Antiarrhythmics
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P9/08—Vasodilators for multiple indications
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- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/02—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
- C07C233/04—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with carbon atoms of carboxamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C233/05—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with carbon atoms of carboxamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/57—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C233/58—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of rings other than six-membered aromatic rings having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
- C07D307/81—Radicals substituted by nitrogen atoms not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/54—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
- C07D333/58—Radicals substituted by nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/04—Systems containing only non-condensed rings with a four-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/10—One of the condensed rings being a six-membered aromatic ring the other ring being six-membered, e.g. tetraline
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Diabetes (AREA)
- Biomedical Technology (AREA)
- Cardiology (AREA)
- Hematology (AREA)
- Heart & Thoracic Surgery (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Obesity (AREA)
- Psychiatry (AREA)
- Urology & Nephrology (AREA)
- Anesthesiology (AREA)
- Nutrition Science (AREA)
- Vascular Medicine (AREA)
- Child & Adolescent Psychology (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Indole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Furan Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9500238A FR2729147A1 (fr) | 1995-01-11 | 1995-01-11 | Nouveaux composes (hetero) cycliques alkyles, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69605452D1 DE69605452D1 (de) | 2000-01-13 |
| DE69605452T2 true DE69605452T2 (de) | 2000-07-06 |
Family
ID=9475014
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69612022T Expired - Fee Related DE69612022T2 (de) | 1995-01-11 | 1996-01-10 | Alkyl(hetero)cyclische Derivate, Verfahren zu deren Herstellung und sie enthaltende pharmazeutische Zusammensetzungen |
| DE69605452T Expired - Fee Related DE69605452T2 (de) | 1995-01-11 | 1996-01-10 | Alkyl(hetero)cyclische Derivate, Verfahren zu deren Herstellung und sie enthaltende pharmazeutische Zusammensetzungen |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69612022T Expired - Fee Related DE69612022T2 (de) | 1995-01-11 | 1996-01-10 | Alkyl(hetero)cyclische Derivate, Verfahren zu deren Herstellung und sie enthaltende pharmazeutische Zusammensetzungen |
Country Status (19)
| Country | Link |
|---|---|
| US (3) | US5693665A (sv) |
| EP (2) | EP0721947B1 (sv) |
| JP (2) | JPH08239353A (sv) |
| CN (2) | CN1061653C (sv) |
| AT (2) | ATE199715T1 (sv) |
| AU (2) | AU714316B2 (sv) |
| CA (2) | CA2167040C (sv) |
| CY (1) | CY2174B1 (sv) |
| DE (2) | DE69612022T2 (sv) |
| DK (2) | DK0721938T3 (sv) |
| ES (2) | ES2157404T3 (sv) |
| FI (2) | FI960123A (sv) |
| FR (1) | FR2729147A1 (sv) |
| GR (2) | GR3032174T3 (sv) |
| HK (1) | HK1013284A1 (sv) |
| NO (2) | NO313552B1 (sv) |
| NZ (2) | NZ280805A (sv) |
| PT (1) | PT721947E (sv) |
| ZA (2) | ZA96212B (sv) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6043264A (en) * | 1995-01-06 | 2000-03-28 | Toray Industries, Inc. | Benzene-condensed heterocyclic derivatives and their uses |
| US5753709A (en) * | 1995-06-07 | 1998-05-19 | Bristol-Myers Squibb Company | N-acyl-2 aryl cyclopropylmethylamine derivatives as melatonergics |
| US5708005A (en) * | 1995-06-27 | 1998-01-13 | Takeda Chemical Industries, Ltd. | Quinolines, their production and use |
| EP0848699B1 (en) * | 1995-07-26 | 2001-10-24 | Takeda Chemical Industries, Ltd. | Benzocycloalkene compounds with melatonine receptor binding affinity, their production and use |
| FR2763335B1 (fr) * | 1997-05-16 | 2000-11-24 | Adir | Nouveaux composes heterocycliques substitues, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| KR100572900B1 (ko) * | 1997-08-07 | 2006-04-24 | 후지모토 쿄다이 가부시키가이샤 | 에틸아민 유도체 |
| FR2771739B1 (fr) * | 1997-11-28 | 2001-04-20 | Adir | Nouveaux composes naphtaleniques, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| FR2772766B1 (fr) * | 1997-12-24 | 2000-06-30 | Adir | Nouveaux composes heterocycliques, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| FR2784375B1 (fr) * | 1998-10-12 | 2000-11-24 | Adir | Nouveaux derives cycliques a chaine cycloalkylenique, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| FR2795323B1 (fr) * | 1999-06-23 | 2001-11-16 | Adir | Utilisation de ligands melatoninergiques pour l'obtention de compositions pharmaceutiques destinees a la prevention ou au traitement des pathologies du systeme gastrointestinal |
| JP4877679B2 (ja) * | 1999-09-03 | 2012-02-15 | 雪印種苗株式会社 | 植物成長調整剤 |
| US6822101B2 (en) | 2002-09-16 | 2004-11-23 | Abbott Laboratories | Process for preparing amine-substituted benzofurans |
| WO2004024707A2 (en) * | 2002-09-16 | 2004-03-25 | Abbott Laboratories | Process for preparing amine type substituted benzofurans |
| FR2853649B1 (fr) * | 2003-04-09 | 2006-07-14 | Servier Lab | Nouveaux derives d'isoquinoleine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| US7393865B2 (en) | 2004-06-17 | 2008-07-01 | Neurocrine Biosciences, Inc. | Sleep inducing compounds and methods relating thereto |
| FR2942625B1 (fr) * | 2009-03-02 | 2013-11-22 | Centre Nat Rech Scient | Derives indoliques pour le traitement de maladies neurodegeneratives |
| US11590663B2 (en) | 2020-01-14 | 2023-02-28 | International Business Machines Corporation | Virtual reality enabled activity allocation |
| RU2750418C1 (ru) * | 2020-11-20 | 2021-06-28 | Виктор Владимирович Яснецов | Средство, обладающее противогипоксической, антиамнестической и нейропротекторной активностью |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3226402A (en) * | 1965-12-28 | And process of making and using same | ||
| US3407210A (en) * | 1961-11-03 | 1968-10-22 | Byk Gulden Lomberg Chem Fab | Aminoethyl-benzofurans and derivatives thereof |
| FR2658818B1 (fr) * | 1990-02-27 | 1993-12-31 | Adir Cie | Nouveaux derives a structure naphtalenique, leur procede de preparation et les compositions pharmaceutiques qui les contiennent. |
| FR2680366B1 (fr) * | 1991-08-13 | 1995-01-20 | Adir | Nouveaux derives d'arylethylamines, leurs procedes de preparation et les compositions pharmaceutiques qui les contiennent. |
| FR2680507B1 (fr) * | 1991-08-23 | 1993-10-08 | Adir Cie | Nouvelles naphtylethylurees et naphtylethylthiourees, leur procede de preparation et les compositions pharmaceutiques qui les contiennent. |
| FR2689124A1 (fr) * | 1992-03-27 | 1993-10-01 | Adir | Nouvelles naphtylalkylamines, leur procédé de préparation et les compositions pharmaceutiques qui les contiennent. |
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1995
- 1995-01-11 FR FR9500238A patent/FR2729147A1/fr active Granted
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1996
- 1996-01-09 AU AU40894/96A patent/AU714316B2/en not_active Ceased
- 1996-01-09 AU AU40893/96A patent/AU694588B2/en not_active Ceased
- 1996-01-10 US US08/584,465 patent/US5693665A/en not_active Expired - Fee Related
- 1996-01-10 NZ NZ280805A patent/NZ280805A/en unknown
- 1996-01-10 DE DE69612022T patent/DE69612022T2/de not_active Expired - Fee Related
- 1996-01-10 ES ES96400052T patent/ES2157404T3/es not_active Expired - Lifetime
- 1996-01-10 DE DE69605452T patent/DE69605452T2/de not_active Expired - Fee Related
- 1996-01-10 CN CN96100856A patent/CN1061653C/zh not_active Expired - Fee Related
- 1996-01-10 CN CN96100335A patent/CN1067678C/zh not_active Expired - Fee Related
- 1996-01-10 DK DK96400051T patent/DK0721938T3/da active
- 1996-01-10 EP EP96400052A patent/EP0721947B1/fr not_active Expired - Lifetime
- 1996-01-10 FI FI960123A patent/FI960123A/sv not_active IP Right Cessation
- 1996-01-10 NO NO19960108A patent/NO313552B1/no unknown
- 1996-01-10 PT PT96400052T patent/PT721947E/pt unknown
- 1996-01-10 ES ES96400051T patent/ES2142550T3/es not_active Expired - Lifetime
- 1996-01-10 FI FI960124A patent/FI960124A/sv not_active IP Right Cessation
- 1996-01-10 DK DK96400052T patent/DK0721947T3/da active
- 1996-01-10 EP EP96400051A patent/EP0721938B1/fr not_active Expired - Lifetime
- 1996-01-10 AT AT96400052T patent/ATE199715T1/de not_active IP Right Cessation
- 1996-01-10 AT AT96400051T patent/ATE187438T1/de not_active IP Right Cessation
- 1996-01-10 NZ NZ280806A patent/NZ280806A/en unknown
- 1996-01-10 NO NO19960109A patent/NO312897B1/no unknown
- 1996-01-11 CA CA002167040A patent/CA2167040C/fr not_active Expired - Fee Related
- 1996-01-11 US US08/584,466 patent/US5703121A/en not_active Expired - Fee Related
- 1996-01-11 JP JP8002721A patent/JPH08239353A/ja active Pending
- 1996-01-11 ZA ZA96212A patent/ZA96212B/xx unknown
- 1996-01-11 ZA ZA96213A patent/ZA96213B/xx unknown
- 1996-01-11 CA CA002167039A patent/CA2167039C/fr not_active Expired - Fee Related
- 1996-01-11 JP JP00272696A patent/JP3790289B2/ja not_active Expired - Fee Related
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1997
- 1997-03-26 US US08/826,340 patent/US5780512A/en not_active Expired - Fee Related
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1998
- 1998-12-22 HK HK98114617A patent/HK1013284A1/xx not_active IP Right Cessation
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1999
- 1999-12-17 GR GR990403260T patent/GR3032174T3/el unknown
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2000
- 2000-05-30 CY CY0000021A patent/CY2174B1/xx unknown
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2001
- 2001-04-27 GR GR20010400637T patent/GR3035789T3/el not_active IP Right Cessation
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